Casco Bay Island Communities

Peaks Island

Peaks Island is located in Casco Bay off of Portland, Maine.

Chebeague Island | Long Island | Peaks Island | Cliff Island
Great Diamond Island & Little Diamond Island | Cushing Island | DirectoryMap

Casco Bay fronts Maine’s largest and most dynamic city, Portland. Visitors come to dine in fine restaurants, explore the historic Old Port and revel in the sophisticated art scene. But this city and neighboring areas are jumping off points for visiting the scores of islands strung along the coast like a many jeweled necklace. Some are lightly populated by artists, fishermen and nature lovers; others are the quiet domains of Maine’s wild coastal creatures

Chebeague Island

Only a ten mile ferry ride from Cousins Island, which connected to the mainland by a bridge at Yarmouth, Chebeague Island is home to some 300 people year round. Chebeague is a Native American word meaning “many springs.” The island does have several underwater springs, some that bubble up to the surface. That and its abundance of wild blueberries are the island’s claim to fame.

The only cars on the island belong to residents, so bring your bicycle or your walking shoes if planning a visit. The lightly populated island is home to deer, raccoons, red foxes and an assortment of land and sea birds. Occasionally seals will nap along one of the rocky beaches. Locals fish from piers and docks, sometimes landing good sized striped bass or bluefish. Lobsters and crabs are also plentiful.

Play a round of golf on the nine-hole golf course, visit the Chebeague Museum in the one time schoolhouse or enjoy a picnic lunch from the Clam Shack. Services include a taxi company, one gas pump, souvenir shops, the Doughty’s Island Market and the library, which does offer wireless Internet access. The Chebeague Island Inn, rustic but comfortable, offers accommodations, or you may be able to rent a cottage or vacation home.

Long Island

Less than 300 people call Long Island home year-round, but in the summer that population more than doubles. First settled in 1732, the largely privately owned island was once a United States Navy Base during World War II, housing a Torpedo Control Officers School and a seaplane base. Information on this era and more is found at the Long Island Historical Society in the Community Center near the Mariner’s Wharf.

Only a 45 minute ride from Portland on the Casco Bay Ferries, visitors come to enjoy South Beach, also called Sandy Beach, hike the Conservation area and the rocky ridge along the island’s eastern end. The 4th of July is a big day on the island, featuring a parade of vintage cars, fire engines, homemade floats and the crowning of Mr. and Ms. Long Island.

Accommodations are available at a few B&B’s or through private vacation home rentals. The Fern Park Lobster Store, Captain Perry’s Café, the Long Island Store and an assortment of art boutiques are available.

Peaks Island

This is an island of movie stars and artists, of budding theatrical productions and protected open spaces preserving native forests for all time. Martin Landau, famed for his “Mission Impossible” role and Jean Stapleton, Edith on “All in the Family” both got their start at Peaks Island’s Greenwood Garden playhouse.

Only three miles from the center of Portland, the island is reachable by the Casco Bay Ferry, allowing passengers and vehicles, or by private boat. Cars are allowed on the island but things get a bit crowded during the busy summer season. Bike and kayak rentals are available. Most accommodations are private vacation homes and cottage rentals but the Inn on Peaks Island offers rooms as well as a local pub frequented by residents. Peaks Island House offers rooms with private ocean view decks and an upstairs restaurant. Both inns are within a five minute walk of the ferry docks.

The tourist friendly island features a number of events including the Annual Peaks Fest in May, a music festival and the Color of Peaks Art Show held both in June and July. The athletic minded island also hosts the Peaks to Portland Swim and the Peaks Island Road Race, on consecutive weekends in July. Outdoor lovers will find plenty of nature trails and picnic spots at the Peaks Island Land Preserve.

Great Diamond Island & Little Diamond Island

Also connected to the mainland by the Casco Bay Ferry is Great Diamond Island. Less than 100 people live on the island year round, getting about mostly by bicycles and golf carts. Prior to World War II, this was a military base, which after decommissioning sat idle for more than 30 years.

The largest development on the island is Diamond Cove, a gated community sitting on the grounds of the former army barracks. Diamond Cove briefly served as an artist community, hosting celebrities such as Harriet Beecher Stowe and Henry Wadsworth Longfellow. Tours of the grounds are sometimes offered, by reservation, other than that the property is closed to the public. Homes sometimes come up for sale and there are a few seasonal rentals offered. Other than this, there are a few private homes near the waterfront.

The Diamond Cover General Store and the Diamond Edge Restaurant are both open from Memorial Day until after Labor Day. Both are local hangouts, but visitors from Portland make regular journeys to the café to dine on their famous Lobster Rolls.

Little Diamond Island is even smaller, and quieter. Formerly known as Little Hog Island, most of it is privately owned. Vacation cottages are available for rent during the summer season, but these are snapped up quickly. The Casco Bay Ferry does offer service year-round, more frequently in the summer. There are no restaurants or services. It is possible to walk to Little Diamond Island from Great Diamond Island via a sandbar at low tide. It is barely a quarter mile from one island to the other; just keep track of the incoming tide so you don’t get stranded.

Cliff Island

Shaped like a lopsided “H” and home to less than 60 fulltime residents, Cliff Island’s claim to fame is being the back drop for the film “The Whales of August.” The 1987 movie featured Hollywood greats such as Bette Davis, Ann Sothern, Vincent Price and Lillian Gish. The cottage used in the film, owned by the Pitkin family, is a semi-famous landmark. Now people come to stroll the beaches, take in the ocean air and just commune with nature.

There are no paved roads and no public services except for one small convenience store and a gas pump but plenty of peace and quiet. Even the residents make trips to Portland to buy groceries. Most residents use golf carts to get around, there are few cars. The population increases to about 200 during the summer when part-time residents come back for the season. Summer rental cottages are sometimes available, but book early because they fill up fast.

Cushing Island

Another quiet island, home to roughly 45 seasonal families, offers summer rentals, miles of hiking trails and more birds than people. The island is off-limits unless you are a local resident or renting a summer cottage. Passenger only ferry service is available from Long Wharf in Portland. A caretaker meets you at the ferry and transports you and your belongings to your cottage.

Island activities include exploring the Cushing Island Conservation Corporation lands, enjoying the five beaches or playing tennis at the town’s community center. Farm Hill Apiary offers guest tours of their beekeeping operation and sells fresh honey.

Grocery shopping is done in Portland and several stores including Harbor Fish Market, Hannafords and Whole Foods will deliver goods to the ferry boat for transport to the island. Since the caretaker meets all boats on Cushing Island there is not problem getting them to your cottage. The same caretaker and his assistants take care of mowing the lawns and seeing to the weekly garbage and recycling pick up. For the rest of life’s necessities, you are on your own. Relax and enjoy life the way things were in tiny-town America, not so long ago.

Casco Bay Island Directories

Visit the following directories to find lodging, dining, attractions, shops, services and recreational activities in Maine’s Casco Bay area.

Casco Bay Islands Map

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